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2005
Cyanation
O 0273
35- 053
Enantioselective Cyanosilylation of Ketones Catalyzed by a Chiral Oxazaborolidinium Ion. — Chiral oxazaborolidinium triflate (Ib) represents an efficient catalyst
for the cyanosilylation of methyl ketones (II) and (V). The reaction proceeds with a
reactive Ph2MePOTms(N=C:) intermediate generated from TmsCN and Me-POPh2.
Excellent stereoselectivity is achieved for acetophenones containing electron-withdrawing para-substituents (IIc) and (IId), while inferior results and opposite stereoinduction is obtained in the presence of electron-donating aryl substituents [cf. (V)]. The
reaction mechanism is discussed in detail. — (RYU, D. H.; COREY*, E. J.; J. Am.
Chem. Soc. 127 (2005) 15, 5384-5387; Dep. Chem. Chem. Biol., Harvard Univ.,
Cambridge, MA 02138, USA; Eng.) — Mischke
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